


The many firsts of Stiles Stilinski

by Pickl3lily



Category: Teen Wolf (TV)
Genre: Actually being nice to Malia, Happy and angsty ending, Mentioned Derek Hale/Braeden, Mostly canon compliant-ish at start, Moving on and being happy, Multi, Starts off as Stalia, Sterek endgame, eventual Stalia bromance
Language: English
Status: Completed
Published: 2015-08-08
Updated: 2015-08-08
Packaged: 2018-04-13 13:39:59
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,628
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4524120
Author URL: https://archiveofourown.org/users/Pickl3lily/pseuds/Pickl3lily
Summary: <blockquote class="userstuff">
              <p>Starts with the milestones in the Stalia relationship, before developing into a Sterek milestone story. </p><p> </p><p>OR:<br/>The many firsts Stiles experiences starting with losing his virginity in the basement of Eichen house.</p>
            </blockquote>





	The many firsts of Stiles Stilinski

**Author's Note:**

> Roughly half of this is Stalia, not because I ship them, but because I felt like sticking close-ish to canon before making the Teen Wolf world a better place. :) Please, try to give it a go, or just skip to about half way through. Or don't. Free will, and all that...

The first time they had sex, they were both cold, scared and a little out of their minds; they both consented, both wanted it but neither of them really intended for anything other than comfort to come out of it.

The first time they cuddled, it was right afterwards; his smile was genuine, the voices in his head, dulled and he felt pleasantly like floating – it wasn’t his first orgasm, that had been when he was twelve, and the sensation itself wasn’t all that different, not quite as amazing as he had thought it would be. But he felt safe in that moment, and the press of someone else’s body, the comfort of having a friend was what they both needed.

The first time he put her above himself, he still wasn’t sure if he’d made the right decision; he had allowed the nogitsune to take control, and he would never forget the deaths that followed, the pain that had been caused. He was glad she was alive, but it was still impossible to be completely certain that his choice had been the right one, but there was no changing it now – it was done, and he had saved her.

The first time she comes through his window, he accidentally calls her Derek, because he’s almost always the only one to do so – this mistake spurs the second time that they have sex, and the first time in his bed; her possessiveness is evidenced by the long gashes he wears across his back, oddly not from the sex but from the first time she acts as the big spoon.

The first time he realises they’re dating, it doesn’t shock him as much as it would have done a year ago; it’s just a realisation that he doesn’t want her to be with anyone else, and when he leans over to press his lips to hers, it becomes the first time that he thinks of her as his girlfriend.

Their first breakup is over his lies, though he wishes he could blame Peter, and he tries to rationalise it, but in the end, it doesn’t matter – he just wants to fix it. Their reunion in the hospital, is shortly followed by the first time they say ‘I love you’.

After Mexico is actually the first time that they make love, and somehow its more awkward than all the other times they’ve had sex – Malia doesn’t really know how to be tender, but she tries, and despite the unusual amount of fumbling, for them, in that moment, its perfect.

The first time he doubts their relationship, is when he fails to tell her about Donovan; he wants to, and he knows that she of all the pack members would understand, but he can’t. He knows the moment that she hears the lie, the uptick of his heartbeat, and waits for her to call him out on it as usual – but she doesn’t. He knows that Malia doesn’t have many tells, but he knows the ones that she does, and he knows when she’s, very rarely, hiding something – like now. The doubt comes from realising that neither one can confide in the other, and yet she seemed to have shared her secret with Theo, (of all people), while he had been speaking with Braeden to help him through, knowing that the mercenary would be able to understand the importance of self-defence.

Their first _real_ fight, is over a kiss. Theo kissed her as Stiles rounded the corner, and after a few seconds she pulled away, allowing her claws to swipe nasty lines across his face; she stops Stiles from doing anything to Theo, ushering him away and not slowing down until they were in Stiles’ room with the door locked. They argue, and its ugly; Stiles knows that she stopped it, he saw that, but he also saw her kiss back, even if it was briefly. He accuses her of having feeling for the werewolf and she doesn’t deny it, countering it with snarls of accusation – Lydia’s scent was all over him, and she knew he still liked her. The argument was petty, blown out of proportion and so ridiculously normal, that the two of them secretly felt some sick sense of pleasure out of it – able to pretend they were a normal couple, with normal issues.

This argument led to their second, and final, break-up, and their first, and also last, round of break-up sex. Malia scratched at him ferociously and for once, he gave back as good as he got, not that it mattered with her healing. The two of them waited until the dread doctors had been dealt with before they revealed their break up to the pack, and having been somewhat estranged since then, they reunited in order to lament how irritated they were at the pack’s attempts to counsel them back together.

The first time they really talked about it, had been awkward to say the least, but they still loved each other, platonically now, and decided to wade through the awkward in order to prevent losing one another from their lives. Their friendship was tentative at first, but as soon as they grew past the awkward tension, their bromance was almost at a point where it could rival the one he shared with Scott.

 

The first time Stiles dated a guy, he realised from the shocked looks on the pack’s faces that he had forgotten to tell them of his bisexuality. He was grateful when Malia, perhaps unintentionally jumped to his defence; she announced her new relationship with gusto, smiling up at the pack wearing that same expression as when she was taking social cues from others, and had seemingly just realised that announcing relationships was what you did amongst friends.

The first time the pack realises that the pair have truly moved on, is when they’re 23 and Stiles agrees to be her maid of honour, despite Lydia’s grumbling of having been passed over for the role. Its also the first time in six years that Derek comes back to Beacon Hills with the intention of staying.

The first time that Derek asks Stiles out, it actually happens by accident – he mentions wanting to go to the new Italian restaurant and Stiles respinds with a wide grin, a peck on the cheek and a jovial “It’s a date!” thrown over his shoulder in parting. Derek makes the mistake of telling Stiles this during said first date, and almost doesn’t get a second, before assuring Stiles that, although at first he just hadn’t wanted to seem rude by rescinding his (accidental) offer, he was enjoying himself and for the first time since his and Braeden’s painfully amicable breakup, he was actually willing to try a relationship.

The first time Stiles mentions that Derek had never seemed bisexual before, Derek closes down and they don’t talk for a day before Derek is crawling through Stiles’ window, just like old times, and confessing that his one male relationship – with Camden Lahey of all people, had not ended well. It had been the most normal breakup of them all, but he still remembered the was Camden has projected his internalised homophobia onto Derek, before leaving to join the forces. It’s how Derek had known to find Isaac; new alpha Derek had checked in on the family of the boy he’d once loved, just to find Camden’s shy but loveable younger brother a shell compared to how he had been when Derek had known him. Isaac didn’t really remember him, but that didn’t matter - all that really mattered was the gift Derek could give him.

Every first with Derek, is more terrifying but more intense than they had been with Malia; he had never stopped caring for her, the two still very close, but some couples would never have the great love that he shared now with Derek.

The first kiss? Had rendered them breathless, despite it being soft and tender, slow and earnest. The first time they had had sex? Had been three months into the relationship – amazingly – they had already said their love declarations, and it had also been the first time they had made love, slow and tender. It was still slightly awkward, as Stiles was involved and aging hadn’t lessened his flailing limbs, but the moment had been so perfect that Stiles had manoeuvred himself into the little spoon position so that Derek wouldn’t see the tears trailing down his cheeks, knowing that the werewolf would probably mistake their meaning. They both took another first just a month later – moving in with a significant other being something that neither had never really done.

 

The first time Stiles proposed, Derek said no. They had been fighting a kanima next to a lake, and the déjà vu of it all had made Stiles sentimental and he had thought it to be the perfect time to ask; it hadn’t been planned, he had had no previous intention of proposing but the rejection stung anyway. He understood the rejection when they returned home and Derek pulled a ring box from the dresser.

The first time Derek proposes, it is perfect; there is a speech and roses – a portion of curly fries too, but still sore from the earlier rejection, and still a petty, sarcastic shit, he says no. They both end up asking each other in unison at midnight on New Year’s two weeks later.

 

The first marriage they have, is also their last; they never divorce and when still human Stiles dies in his sleep sixty years later, Derek chooses to stop fighting for the first time, and after sorting his affairs and being fully at peace, allows his body to succumb to its weariness a year later.

 

 

**Author's Note:**

> Yeah, so I have always believed that Malia would have been more awesome and more popularly received had she been developed as a character before being put into a relationship, and so I decided to write a fic where they actually had a good relationship, and it ends the way a lot of relationships do. 
> 
> This is Sterek endgame, because no matter how hard I try, if I'm unprompted, my ideas always drift back here. Hope you guys enjoy it, and feel free to leave kudos if you enjoy and leave feedback if you want. :)


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